HCID 22319036, compound → HCID 22319111, compound

HRID 497826Notes

Reaction equation

HRID 497826 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:28])[N:10]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:13]=1>Br.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:28])[N:10]([C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:13]=1

Participants

4

Reactant 1

HCID 22319036HCID 22319036, compound

Product 1

HCID 22319111HCID 22319111, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(2-Chlorophenyl)-5-(2-pyridyl)-1-(4-methoxyphenyl)-1,2-dihydropyridin-2-one (440 mg) was dissolved in 5 ml of 48% hydrobromic acid and heated to reflux for 1 hours. After the reaction solution was allowed to cool at room temperature, it was diluted with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated in vacuo and purified by a silica gel column chromatography (hexane-ethyl acetate system) to give 292 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated in vacuo
  8. custompurified by a silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-446e8b48f84f4a4e9bbf61fb58794210
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

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